A method that subjects an olefin and an alcohol to an addition reaction in the presence of a solid acid catalyst to produce an ether has been known. For example, Patent Document 1 discloses a method that utilizes a crystalline aluminosilicate as a catalyst. Patent Document 2 discloses a method that utilizes a special aluminosilicate having a large number of outer-surface acid sites as a catalyst. Patent Document 3 discloses a method that utilizes a heteropolyacid that includes tungsten oxide (for which the average number of crystal water molecules has been adjusted to 3.0 or less per molecule of the heteropolyacid) as a catalyst. Patent Document 4 discloses a method that utilizes an acidic ion-exchange resin having a water content of 5 mass % or less as a catalyst.
However, when producing a cycloalkyl alkyl ether on an industrial scale from an alicyclic olefin (starting material) using the above solid acid catalyst, deterioration in catalytic activity occurs with the passing of time during long-term continuous operation. Therefore, it is necessary to frequently regenerate the catalyst that has deteriorated in activity, or additionally supply or exchange the catalyst.
Patent Document 5 proposes a method that uses an alicyclic olefin having a linear conjugated diene compound content of 10 ppm or less as the raw material, and Patent Document 6 proposes a method that uses an alicyclic olefin having a linear conjugated diene compound content of 10 ppm or less and a cyclic conjugated diene compound content of 10 ppm or less as the raw material in order to solve the above problem.
These methods can suppress deterioration in catalytic activity with the passing of time, but are not necessarily satisfactory in terms of reaction efficiency and productivity.